Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Shulgin, Alexander T.; Sargent, T.; Naranjo, Claudio A.

doi:10.1159/000136416

Cited by 13 publications

(11 citation statements)

References 10 publications

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“…During the mid‐1960s, Shulgin initiated tests on the psychotherapeutic potential of MDA and MMDA with psychotherapist Claudio Naranjo MD at the Department of Anthropological Medicine, University of Chile (Santiago de Chile) [27,28]. The results were favourable and were published in 1967 on MDA [29] and in 1973 on MMDA [28,30].…”

Section: On the Possible Role Of Mda Mmda And Mde In The History Of mentioning

confidence: 99%

Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin

Benzenhöfer

Passie

2010

Addiction

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Shulgin was not the first to synthesize MDMA, but he played an important role in its history. It seems plausible that he was so impressed by its effects that he introduced it to psychotherapist Zeff in 1977. This, and the fact that in 1978 he published with David Nichols the first paper on the pharmacological action of MDMA in humans, explains why Shulgin is sometimes (erroneously) called the 'father' of MDMA.

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Section: On the Possible Role Of Mda Mmda And Mde In The History Of mentioning

confidence: 99%

Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin

Benzenhöfer

Passie

2010

Addiction

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“…The appropriate choice of numbers will be determined by the location of substituents R7, R8, and R9. Both isomers and their various methoxy derivatives (R7, R8, and R9, see the following) [1,2,11,25] appear to stimulate hallucinogenic/psychotomimetic activity to some degree.…”

Section: Alteration Of the Alkyldioxy Bridge (R4 R5 R6)mentioning

confidence: 99%

“…Addition of one methoxy group (R7 = OCH3, R8 = R9 = H) in either ortho ring position (2-methoxy or 6-methoxy) greatly increases the hallucinogenic activity of MDA [1,2,11,27,28]. Meta substitution (5-methoxy) produces a less potent isomer [1,2,11,27,28] having CNS effects which could not be accurately defined as either psychotomimetic or hallucinogenic [25]. Putting a methoxy group at the 2 position of the homolog MDPEA yields a "mood elevator" [1] of greater activity than 3,4-MDA; a methoxy group at the 5 position decreases the psychotomimetic activity induced by this substituent [1,2].…”

Section: Ring Substitution (R7 R8 R9)mentioning

confidence: 99%

An Evaluation of the Potential for Clandestine Manufacture of 3,4-Methylenedioxyamphetamine (MDA) Analogs and Homologs

Cason

1990

Journal of Forensic Sciences

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Encountering a novel controlled-substance analog (designer drug) has become a distinct possibility for all forensic drug laboratories. 3,4-Methylenedioxyamphetamine (MDA) in particular is a receptive parent compound for the molecular modifications which produce such homologs and analogs. The identification of these compounds, however, can prove to be an arduous task. It would be desirable to direct the focus of the identification to those compounds which are the more likely candidates for clandestine-laboratory synthesis. The process of narrowing the range of theoretical possibilities to logical choices may be enhanced by using a suitable predictive scheme. Such a predictive scheme for MDA analogs is presented based on putative Central Nervous System activity, existence or formulation of a reasonable synthesis method, and availability of the required precursors.

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“…In 1947 researchers produced the first psychoactive analogue of mescaline, TMA (3,4,5-trimethoxyamphetamine), with twice the psychoactive potency of mescaline (Shulgin et al 1973). Although peyote has been recognised for its psychoactive properties for centuries, it was not until 1896 that the structure of mescaline was identified, and subsequently synthesised in 1918.…”

Section: Mescaline Analogues (Phenylethylamines)mentioning

confidence: 99%

‘Designer Drugs’

Buchanan

Brown

1988

Medical Toxicology

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'Designer drugs' are substances intended for recreational use which are derivatives of approved drugs so as to circumvent existing legal restrictions. The term as popularised by the lay press lacks precision. Contrary to the popular belief that 'designer drugs' are original creations, the majority of these agents are 'borrowed' from legitimate pharmaceutical research. They merely represent the most recent developments in the evolution of mind-altering chemicals. The most extensively studied class of psychoactive compounds is the phenylethylamines (mescaline analogues). This class includes catecholamines, therapeutic agents and numerous illicit derivatives. Subtle alterations of the phenylethylamine molecule give rise to a spectrum of pharmacological properties ranging from pure sympathomimetic stimulation to primarily psychoactive effects. Although most of these compounds are only of historical interest, amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine (MDA), and 3,4-methylenedioxymethamphetamine (MDMA) continue to be used recreationally. Many deaths have been ascribed to this class of compounds. In overdose the differences between these compounds blur and the clinical presentation is similar to that of amphetamine overdose characterised by tachycardia, hypertension, hyperthermia, diaphoresis, mydriasis, agitation, muscle rigidity, and hyper-reflexia. Death usually results from arrhythmias, hyperthermia or intracerebral haemorrhage. Treatment is aggressive and supportive with careful attention to temperature, blood pressure and seizure control. Synthetic opioid derivatives, which represent the second major class of 'designer drugs', are derivatives of fentanyl (e.g. alpha-methylfentanyl, 3-methylfentanyl) or pethidine (meperidine) and are extremely potent compounds responsible for numerous overdose deaths. Attempts to synthesise pethidine have resulted in the accidental production of MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine), a compound which is metabolised in the brain by the monoamine oxidase system to a toxic intermediate (MPP+) which selectively destroys the sustantia nigra, resulting in the rapid onset of severe Parkinsonian symptoms. Naloxone will antagonise the opiate effects of this drug class, although high doses may be required. Arylhexylamines constitute the third class of 'designer drugs'. The predominant member of this class is phencyclidine (PCP), a derivative of the anaesthetic ketamine. This unique class of psychoactive agents exhibits broad and complex pharmacological effects.(ABSTRACT TRUNCATED AT 400 WORDS)

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Animal Pharmacology and Human Psychopharmacology of 3-Methoxy-4,5-Methylenedioxyphenylisopropylamine (MMDA)

Cited by 13 publications

References 10 publications

Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin

Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin

An Evaluation of the Potential for Clandestine Manufacture of 3,4-Methylenedioxyamphetamine (MDA) Analogs and Homologs

‘Designer Drugs’

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